Showing metabocard for PC(22:0/22:1(13Z)) (BMDB0008546)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:23:56 UTC
Update Date2020-06-04 19:47:59 UTC
BMDB IDBMDB0008546
Secondary Accession Numbers
  • BMDB08546
Metabolite Identification
Common NamePC(22:0/22:1(13Z))
DescriptionPC(22:0/22:1(13Z)), also known as PC(22:0/22:1) or gpcho(44:1), belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(22:0/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(22:0/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(22:0/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(22:0/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(22:0/22:1(13Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(22:0/22:1(13Z)) can be biosynthesized from CDP-choline and DG(22:0/22:1(13Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(22:0/22:1(13Z)) and L-serine can be converted into choline and PS(22:0/22:1(13Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(22:0/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:0/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(22:0/22:1(13Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Behenoyl-2-erucoyl-sn-glycero-3-phosphocholineHMDB
PC(22:0/22:1)HMDB
GPCho(44:1)HMDB
Phosphatidylcholine(22:0/22:1)HMDB
PC(44:1)HMDB
LecithinHMDB
GPCho(22:0/22:1)HMDB
1-Docosanoyl-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(44:1)HMDB
PC(22:0/22:1(13Z))Lipid Annotator
Chemical FormulaC52H102NO8P
Average Molecular Weight900.3419
Monoisotopic Molecular Weight899.734305757
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-(docosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C52H102NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,50H,6-20,22,24-49H2,1-5H3/b23-21-/t50-/m1/s1
InChI KeyLTXUEXPDKWPLQA-ZMGYLBOHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.83ALOGPS
logP13.09ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count51ChemAxon
Refractivity272.19 m³·mol⁻¹ChemAxon
Polarizability115.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-9eab8c2a4eceebf93aa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000009-dad545d1fe3969a8f0d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900040121-c0a22f85c412a92bbb44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000009-449b3d3a16cc27cb0229View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000019-c0b2dfe60a94ef3a3fe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000k-0900063911-2337f8b20d4eed41f684View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000009-57fc9e453b3cdb3ad04dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0003000009-dcaa9a8a98b9c3243807View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0009000004-696169491cec61629eebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-e6180050699348029b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000009-3ad68bd421552c90533eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900040121-7a1e215b860c1850c45dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-95ccde9ff1a9849e3ba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f72-0008000290-78109335789336693101View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1009200000-2b79d859ac8f15bd335bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-ed9ede0f6ea36f3c9a39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000019-6d75a94dcb3169a1d65dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-060r-0100090511-2d3352d3ef75ab7a706bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified1.39 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.25 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.16 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008546
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779119
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.